Anti-plant-virus agent

ABSTRACT

The present invention provides an anti-plant virus agent which exhibits preventative and therapeutic effects on plant virus diseases. The anti-plant virus agent of the present invention is characterized by containing at least one compound selected from the group consisting of ascorbic acid derivatives represented by Formula (I) (wherein, R 1  to R 4  each independently represents a hydrogen atom, —SO 3 H, —PO 3 H 2 , a glycosyl group, or —COR 11 , wherein R 11  represents an unsubstituted or substituted C1-30 alkyl group, or an unsubstituted or substituted C2-30 alkenyl group, with the proviso that R 1  to R 4  may not all be hydrogen atoms at the same time), and salts thereof.

TECHNICAL FIELD

The present invention relates to an anti-plant virus agent. More specifically, the present invention relates to an anti-plant virus agent which exhibits preventative and therapeutic effects on plant virus diseases showing symptoms such as yellow mosaic of new leaves, leaf curling, or plant stunting.

Priority is claimed on Japanese Patent Application No. 2009-211649, filed on Sep. 14, 2009, the content of which is incorporated herein by reference.

BACKGROUND ART

Plants which are grown on agricultural land or general households are often infected with plant viruses, and as a result, the value of commodities, production amounts and appearance, and the like, as an agricultural crop, may be remarkably decreased. Plant virus diseases may cause serious damage to important crops such as grains, vegetables, and fruit trees. Viruses which have invaded plant cells proliferate entirely relying on the metabolisms of the host plants. For this reason, it is difficult to specifically inhibit only the proliferation of the viruses whilst maintaining the normal metabolic pathways in plants. Therefore, plant virus diseases have been diseases which are difficult to be controlled.

Several control agents against plant virus diseases have been proposed. For example, Patent Literature 1 discloses a composition which contains antibacterial antibiotics such as neomycin sulfate and organic acids such as ascorbic acid, and states that the composition is capable of inhibiting plant diseases. In addition, in Patent Literature 1, the ascorbic acid is used for playing a role in assisting the antibacterial substances.

However, anti-plant virus agents which have been proposed hitherto have problems such as in the productivities thereof, in actual inhibitive effects against plant diseases, and safety in animals and plants, and most of them have not been put to practical use. In addition, while anti-plant virus agents which exhibit preventive effects have been proposed, very few anti-plant virus agents which exhibit therapeutic effects have been proposed.

On the other hand, ascorbic acid (vitamin C) or ascorbic acid derivatives have been used for medicines, cosmetics, food, and feedstuffs, and the like. In addition, the use thereof in the prevention of blemishes or freckles, and the like, from a suntan, and the use thereof as a hair growth agent have been proposed (refer to Patent Literatures 2 and 3). However, use of ascorbic acid derivatives for controlling plant diseases is not known.

CITATION LIST Patent Literature

-   [Patent Literature 1] PCT Japanese Translation Patent Publication     No. 2001-508808 -   [Patent Literature 2] Japanese Unexamined Patent Application     Publication No. 2000-351905 -   [Patent Literature 3] Japanese Unexamined Patent Application     Publication No. 2001-354522

SUMMARY OF INVENTION Technical Problem

The object of the present invention is to provide an anti-plant virus agent which exhibits preventative and therapeutic effects on plant virus diseases.

Solution to Problem

As a result of intensive studies to solve those problems, the present inventors have found that when ascorbic acid, which has a low antiviral activity and which also had been used only for playing a role in assisting antimicrobial compounds or antibiotics as a main component, is esterified or glycosylated with a specific compound, the compound has a high anti-plant viral activity. The present invention has been completed by further studies based on these findings.

That is, the present invention is directed to an anti-plant virus agent which contains at least one compound selected from the group consisting of ascorbic acid derivatives represented by Formula (I) and salts thereof:

wherein, R¹ to R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹, wherein R¹¹ represents an unsubstituted or substituted C1-30 alkyl group, or an unsubstituted or substituted C2-30 alkenyl group, with the proviso that R¹ to R⁴ may not all be hydrogen atoms at the same time.

It is preferable that in Formula (I), R¹ and R² represent a hydrogen atom, and R³ and R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹, wherein R¹¹ represents the same meaning as described above.

In addition, it is also preferable that in Formula (I), R¹ be —COR¹¹, wherein R¹¹ represents the same meaning as described above, and R² to R⁴ represent a hydrogen atom.

Advantageous Effects of Invention

The anti-plant virus agent of the present invention has a high anti-plant viral activity. The application of the anti-plant virus agent of the present invention to normal plants makes it possible to effectively prevent infection by plant viruses (preventive effect). In addition, the application of the anti-plant virus agent of the present invention to plants infected with plant viruses makes it possible to suppress the onset of plant diseases (therapeutic effect).

DESCRIPTION OF EMBODIMENTS

Hereinafter, the present invention will be described in detail.

The anti-plant virus agent of the present invention contains at least one compound selected from the group consisting of the ascorbic acid derivative represented by Formula (I) and the salts thereof. In addition, the ascorbic acid derivative of the present invention has a meaning of embracing any one of two isomers of L-ascorbic acid derivatives and isoascorbic acid derivatives, or a mixture thereof.

The ascorbic acid derivatives used in the present invention are those in which in Formula (I), R¹ to R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹ with the proviso that R¹ to R⁴ may not all be hydrogen atoms at the same time.

A glycosyl group is a sugar residue such as a monosaccharide or a low-molecular-weight oligosaccharide (specifically, a partial structure of the molecule containing a binding position formed by the removal of a hemiacetal hydroxyl group of the sugar moiety). Examples of the monosaccharide include glucose, galactose, fructose, and rhamnose, and the like, and examples of the oligosaccharide include rutinose, vicianose, lactose, maltose and sucrose, and the like. Therefore, the glycosyl group includes, for example, a glucosyl group, a galactosyl group, a fructosyl group, and a rhamnosyl group, and the like. In addition, the glycosyl group also includes the groups forming disaccharides by the binding of any combination of these glycosyl groups via 1→2 linkage, 1→3 linkage, 1→4 linkage or 1→6 linkage.

R¹¹ represents an unsubstituted or substituted C1-30 alkyl group, or an unsubstituted or substituted C2-30 alkenyl group.

Herein, the term “unsubstituted” means that the relevant group has only a group forming a mother nucleus. In addition, descriptions using only the name of the group forming a mother nucleus without the expression “substituted”, unless otherwise stated, mean “unsubstituted”.

On the other hand, the term “substituted” means that the hydrogen atom of any of the group forming a mother nucleus is replaced with a group which has a different structure from that of the mother nucleus. Therefore, the term “substituent” refers to another group which replaces a group forming a mother nucleus. There may be one or two or more substituents. The two or more substituents may be the same as or different from each other. For example, a substituted C1-30 alkyl group is one in which a group Banning a mother nucleus is a C1-30 alkyl group, and any hydrogen atom of this group is substituted with a group having a different structure (the “substituent”).

The C1-30 alkyl group is a saturated aliphatic hydrocarbon group having 1-30 carbon atoms. The C1-30 alkyl group may be a straight chain or a branched chain.

Specifically, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an n-octyl group, an n-undecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-henicosyl group, an n-triacontyl group, and the like, can be exemplified.

The C2-30 alkenyl group is an aliphatic hydrocarbon group having 2 to 30 carbon atoms and having at least one carbon-carbon double bond. The C2-30 alkenyl group may be a straight chain or a branched chain.

Specifically, a vinyl group, a 1-propenyl group, an allyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 2-pentadecen-8-yl group, and the like, can be exemplified.

Examples of the groups which can be a “substituent” of the C1-30 alkyl group or the C2-30 alkenyl group include a hydroxyl group; a mercapto group; an amino group; a nitro group; a halogen atom such as a chlorine atom, a fluorine atom or a bromine atom; an alkoxy group such as a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group or a t-butoxy group; an aryloxy group such as a phenoxy group or 1-naphthyloxy group; a haloalkoxy group such as a fluoromethoxy group, a difluoromethoxy group, trifluoromethoxy group, a 2-chloroethoxy group, a 2,2,2-trichloroethoxy group or a 1,1,1,3,3,3-hexafluoro-2-propoxy group; an alkylthio group such as a methylthio group or an ethylthio group; an arylthio group such as a phenylthio group or a 1-naphthylthio group; an alkylamino group such as a methylamino group or a diethylamino group; an arylamino group such as an anilino group or a 1-naphthylamino group; and a cyano group, and the like.

The above R¹¹ is preferably an unsubstituted or substituted C8-20 alkyl group, or an unsubstituted or substituted C8-20 alkenyl group. More preferred as R¹¹ are an n-pentyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, and a 9-hexadecenyl group.

One kind of the preferred ascorbic acid derivative used in the present invention includes one wherein R¹ and R² represent a hydrogen atom, and R³ and R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹. Examples of such ascorbic acid derivatives can include ascorbic acid 2-phosphate ester, ascorbic acid 3-phosphate ester, ascorbic acid 2-sulfate ester, ascorbic acid 3-sulfate ester, ascorbic acid 2-glucoside, and the like.

Other kinds of the preferred ascorbic acid derivatives used in the present invention include one wherein R¹ is —COR¹¹, and R² to R⁴ all represent a hydrogen atom. Examples of such ascorbic acid derivatives can include ascorbic acid 6-myristate, ascorbic acid 6-palmitate, ascorbic acid 6-stearate, ascorbic acid 2-myristate, ascorbic acid 2-palmitate, ascorbic acid 2-stearate, ascorbic acid 2,6-dimyristate, ascorbic acid 2,6-dipalmitate and ascorbic acid 2,6-distearate, and the like.

The salts of the ascorbic acid derivatives used in the present invention are not particularly limited, if they are agriculturally and horticulturally acceptable salts. Examples thereof can include alkali metal salts such as sodium salts or potassium salts; and alkali earth metal salts such as calcium salts or magnesium salts, and the like.

The ascorbic acid derivatives and their salts used in the present invention can be obtained by known synthesis methods. For example, —COR¹¹ can be introduced to any of R¹ to R⁴ by an esterification of a fatty acid compound with ascorbic acid. —PO₃H₂ can be introduced to any of R¹ to R⁴ by the esterification of a phosphoric acid compound with ascorbic acid. —SO₃H can be introduced to any of R¹ to R⁴ by the esterification of a sulfuric acid compound with ascorbic acid. In addition, many of the ascorbic acid derivatives used in the present invention are commercially available, and thus, they can be also used.

In addition, the structures of the ascorbic acid derivatives and their salts can be identified and confirmed by known analysis means such as an IR spectrum, NMR spectrum, mass spectrum or elemental analysis. In addition, when a mixture of the ascorbic acid derivative and the salt has been obtained by the above synthesis method, the desired material can be isolated by a known purification method such as extraction, distillation or chromatography.

The anti-plant virus agent of the present invention may contain a compound selected from the group consisting of the aforementioned ascorbic acid derivatives and the salts thereof as an active component, alone or in a combination of two or more thereof.

In addition, the anti-plant virus agent of the present invention may contain other optional components unless an anti-plant viral activity is inhibited by them. Examples of the other optional components can include fillers, extenders, binders, moisturizers, disintegrating agents, lubricants, diluents, excipients, spreading agents, microbicides, fungicides, bactericides, miticides, insecticides, herbicides, growth regulators, solvents, and the like.

In view of the fact that better anti-plant virus agents are obtained, it is preferable that the anti-plant virus agent of the present invention contain a substance which promotes the general resistance of plants against viruses. Examples of the substance promoting such resistance can include microbicides such as probenazole or tiadinil; isonicotinic acid; and salicylic acid, and the like.

In addition, it is preferable that the anti-plant virus agent of the present invention contains a surfactant, so that the ascorbic acid derivatives and the salts thereof can be uniformly dispersed and dissolved in a solvent. Examples of the surfactant can include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, and the like.

The dosage form of the anti-plant virus agent of the present invention is not particularly limited. Depending on the plants to be applied, the dosage form can be appropriately selected from wettable powders, emulsions, water soluble powders, granules, dusts and tablets, and the like. The method for the preparation of the anti-plant virus agent of the present invention is not particularly limited, and can be appropriately selected from the known preparation methods depending on the dosage form.

The application method of the anti-plant virus agent of the present invention is not particularly limited, and can be appropriately determined depending on the nature of each contained component, or the kinds of the plants to be treated, and the like. Preferred examples thereof can include the usage methods by foliage application, dipping treatment, soil irrigation, seed disinfection or smoking, and the like. The anti-plant virus agent of the present invention can be used without being restricted by the type of cultivation such as soil cultivation or hydroponic cultivation. In addition, the agent of the present invention can exhibit an excellent effect even when it is used under a special environment such as a growing point culture.

The application amount of the anti-plant virus agent of the present invention can be appropriately determined depending on weather conditions, the type of formulation, the application period, the application method, the application place, the diseases to be controlled, or the crops to be treated, and the like.

The plants to which the anti-plant virus agent of the present invention can be applied are not particularly limited, and may be either edible plants or non-edible plants. Preferred examples thereof can include woody plants such as cherries or grapes; herbaceous plants such as tobacco or clover; grains such as corn or potatoes; vegetables such as strawberries or radishes; beans such as soybeans or azuki beans; flowering plants such as carnations or roses; and ornamental plants such as daphne.

The plant viruses to be targeted by the anti-plant virus agent of the present invention are not particularly limited. Preferred examples thereof can include geminiviruses having single-stranded DNA genomes, cauliflower mosaic virus having double-stranded DNA genomes, tobacco mosaic virus and tomato bushy stunt virus having single-stranded RNA genomes, and rice ragged stunt virus having double-stranded RNA genomes, and the like.

EXAMPLES

Hereinafter, while the present invention will be more specifically illustrated by way of examples, the scope of the present invention should not be construed as being limited thereto.

(Examples of the Ascorbic Acid Derivatives Used in the Anti-Plant Virus Agent of the Present Invention)

Examples of the ascorbic acid derivatives and the salts thereof, which have been synthesized by the esterification or glycosylation of ascorbic acid, or which are commercially available, are shown in Table 1-1 to Table 1-13. R¹ to R⁴ in the tables correspond to R¹ to R⁴ in Formula (I).

TABLE 1-1 R¹ R² R³ R⁴ 1 SO₃H H H H 2 PO₃H₂ H H H 3 glucosyl H H H 4 mannosyl H H H 5 galactosyl H H H 6 COCH₃ H H H 7 COC₃H₇-i H H H 8 COC₁₇H₃₅-n H H H 9 COC₁₆H₃₃-n H H H 10 COC₁₈H₃₇-n H H H 11 CO(CH₂)₇CH═CHC₆H₁₃-n H H H 12 COCH═CH₂ H H H 13 COCH₂CH═CH₂ H H H 14 H SO₃H H H 15 H PO₃H₂ H H 16 H glucosyl H H 17 H mannosyl H H 18 H galactosyl H H 19 H COCH₃ H H 20 H COC₃H₇-i H H 21 H COC₁₇H₃₅-n H H 22 H COC₁₆H₃₃-n H H 23 H COC₁₈H₃₇-n H H 24 H CO(CH₂)₇CH═CHC₆H₁₃-n H H 25 H COCH═CH₂ H H 26 H COCH₂CH═CH₂ H H 27 H H SO₃H H 28 H H PO₃H₂ H 29 H H glucosyl H 30 H H mannosyl H 31 H H galactosyl H 32 H H COCH₃ H 33 H H COC₃H₇-i H 34 H H COC₁₇H₃₅-n H 35 H H COC₁₆H₃₃-n H

TABLE 1-2 R¹ R² R³ R⁴ 36 H H COC₁₈H₃₇-n H 37 H H CO(CH₂)₇CH═CHC₆H₁₃-n H 38 H H COCH═CH₂ H 39 H H COCH₂CH═CH₂ H 40 H H H SO₃H 41 H H H PO₃H₂ 42 H H H glucosyl 43 H H H mannosyl 44 H H H galactosyl 45 H H H COCH₃ 46 H H H COC₃H₇-i 47 H H H COC₁₇H₃₅-n 48 H H H COC₁₆H₃₃-n 49 H H H COC₁₈H₃₇-n 50 H H H CO(CH₂)₇CH═CHC₆H₁₃-n 51 H H H COCH═CH₂ 52 H H H COCH₂CH═CH₂ 53 SO₃H SO₃H H H 54 SO₃H PO₃H₂ H H 55 SO₃H glucosyl H H 56 SO₃H mannosyl H H 57 SO₃H galactosyl H H 58 SO₃H COCH₃ H H 59 SO₃H COC₃H₇-i H H 60 SO₃H COC₁₇H₃₅-n H H 61 SO₃H COC₁₆H₃₃-n H H 62 SO₃H COC₁₈H₃₇-n H H 63 SO₃H CO(CH₂)₇CH═CHC₆H₁₃-n H H 64 SO₃H COCH═CH₂ H H 65 SO₃H COCH₂CH═CH₂ H H 66 PO₃H₂ SO₃H H H 67 PO₃H₂ PO₃H₂ H H 68 PO₃H₂ glucosyl H H 69 PO₃H₂ mannosyl H H 70 PO₃H₂ galactosyl H H

TABLE 1-3 R¹ R² R³ R⁴ 71 PO₃H₂ COCH₃ H H 72 PO₃H₂ COC₃H₇-i H H 73 PO₃H₂ COC₁₇H₃₅-n H H 74 PO₃H₂ COC₁₆H₃₃-n H H 75 PO₃H₂ COC₁₈H₃₇-n H H 76 PO₃H₂ CO(CH₂)₇CH═CHC₆H₁₃-n H H 77 PO₃H₂ COCH═CH₂ H H 78 PO₃H₂ COCH₂CH═CH₂ H H 79 glucosyl SO₃H H H 80 glucosyl PO₃H₂ H H 81 glucosyl glucosyl H H 82 glucosyl mannosyl H H 83 glucosyl galactosyl H H 84 glucosyl COCH₃ H H 85 glucosyl COC₃H₇-i H H 86 glucosyl COC₁₇H₃₅-n H H 87 glucosyl COC₁₆H₃₃-n H H 88 glucosyl COC₁₈H₃₇-n H H 89 glucosyl CO(CH₂)₇CH═CHC₆H₁₃-n H H 90 glucosyl COCH═CH₂ H H 91 glucosyl COCH₂CH═CH₂ H H 92 COC₁₆H₃₃-n SO₃H H H 93 COC₁₆H₃₃-n PO₃H₂ H H 94 COC₁₆H₃₃-n glucosyl H H 95 COC₁₆H₃₃-n mannosyl H H 96 COC₁₆H₃₃-n galactosyl H H 97 COC₁₆H₃₃-n COCH₃ H H 98 COC₁₆H₃₃-n COC₃H₇-i H H 99 COC₁₆H₃₃-n COC₁₇H₃₅-n H H 100 COC₁₆H₃₃-n COC₁₆H₃₃-n H H 101 COC₁₆H₃₃-n COC₁₈H₃₇-n H H 102 COC₁₆H₃₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H H 103 COC₁₆H₃₃-n COCH═CH₂ H H 104 COC₁₆H₃₃-n COCH₂CH═CH₂ H H 105 CO(CH₂)₇CH═CHC₆H₁₃-n SO₃H H H

TABLE 1-4 R¹ R² R³ R⁴ 106 CO(CH₂)₇CH═CHC₆H₁₃-n PO₃H₂ H H 107 CO(CH₂)₇CH═CHC₆H₁₃-n glucosyl H H 108 CO(CH₂)₇CH═CHC₆H₁₃-n mannosyl H H 109 CO(CH₂)₇CH═CHC₆H₁₃-n galactosyl H H 110 CO(CH₂)₇CH═CHC₆H₁₃-n COCH₃ H H 111 CO(CH₂)₇CH═CHC₆H₁₃-n COC₃H₇-i H H 112 CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₇H₃₅-n H H 113 CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₆H₃₃-n H H 114 CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₈H₃₇-n H H 115 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H H 116 CO(CH₂)₇CH═CHC₆H₁₃-n COCH═CH₂ H H 117 CO(CH₂)₇CH═CHC₆H₁₃-n COCH₂CH═CH₂ H H 118 SO₃H H SO₃H H 119 SO₃H H PO₃H₂ H 120 SO₃H H glucosyl H 121 SO₃H H mannosyl H 122 SO₃H H galactosyl H 123 SO₃H H COCH₃ H 124 SO₃H H COC₃H₇-i H 125 SO₃H H COC₁₇H₃₅-n H 126 SO₃H H COC₁₆H₃₃-n H 127 SO₃H H COC₁₈H₃₇-n H 128 SO₃H H CO(CH₂)₇CH═CHC₆H₁₃-n H 129 SO₃H H COCH═CH₂ H 130 SO₃H H COCH₂CH═CH₂ H 131 PO₃H₂ H SO₃H H 132 PO₃H₂ H PO₃H₂ H 133 PO₃H₂ H glucosyl H 134 PO₃H₂ H mannosyl H 135 PO₃H₂ H galactosyl H 136 PO₃H₂ H COCH₃ H 137 PO₃H₂ H COC₃H₇-i H 138 PO₃H₂ H COC₁₇H₃₅-n H 139 PO₃H₂ H COC₁₆H₃₃-n H 140 PO₃H₂ H COC₁₈H₃₇-H H

TABLE 1-5 R¹ R² R³ R⁴ 141 PO₃H₂ H CO(CH₂)₇CH═CHC₆H₁₃-n H 142 PO₃H₂ H COCH═CH₂ H 143 PO₃H₂ H COCH₂CH═CH₂ H 144 glucosyl H SO₃H H 145 glucosyl H PO₃H₂ H 146 glucosyl H glucosyl H 147 glucosyl H mannosyl H 148 glucosyl H galactosyl H 149 glucosyl H COCH₃ H 150 glucosyl H COC₃H₇-i H 151 glucosyl H COC₁₇H₃₅-n H 152 glucosyl H COC₁₆H₃₃-n H 153 glucosyl H COC₁₈H₃₇-n H 154 glucosyl H CO(CH₂)₇CH═CHC₆H₁₃-n H 155 glucosyl H COCH═CH₂ H 156 glucosyl H COCH₂CH═CH₂ H 157 COC₁₆H₃₃-n H SO₃H H 158 COC₁₆H₃₃-n H PO₃H₂ H 159 COC₁₆H₃₃-n H glucosyl H 160 COC₁₆H₃₃-n H mannosyl H 161 COC₁₆H₃₃-n H galactosyl H 162 COC₁₆H₃₃-n H COCH₃ H 163 COC₁₆H₃₃-n H COC₃H₇-i H 164 COC₁₆H₃₃-n H COC₁₇H₃₅-n H 165 COC₁₆H₃₃-n H COC₁₆H₃₃-n H 166 COC₁₆H₃₃-n H COC₁₈H₃₇-n H 167 COC₁₆H₃₃-n H CO(CH₂)₇CH═CHC₆H₁₃-n H 168 COC₁₆H₃₃-n H COCH═CH₂ H 169 COC₁₆H₃₃-n H COCH₂CH═CH₂ H 170 CO(CH₂)₇CH═CHC₆H₁₃-n H SO₃H H 171 CO(CH₂)₇CH═CHC₆H₁₃-n H PO₃H₂ H 172 CO(CH₂)₇CH═CHC₆H₁₃-n H glucosyl H 173 CO(CH₂)₇CH═CHC₆H₁₃-n H mannosyl H 174 CO(CH₂)₇CH═CHC₆H₁₃-n H galactosyl H 175 CO(CH₂)₇CH═CHC₆H₁₃-n H COCH₃ H

TABLE 1-6 R¹ R² R³ R⁴ 176 CO(CH₂)₇CH═CHC₆H₁₃-n H COC₃H₇-i H 177 CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₇H₃₅-n H 178 CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₆H₃₃-n H 179 CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₈H₃₇-n H 180 CO(CH₂)₇CH═CHC₆H₁₃-n H CO(CH₂)₇CH═CHC₆H₁₃-n H 181 CO(CH₂)₇CH═CHC₆H₁₃-n H COCH═CH₂ H 182 CO(CH₂)₇CH═CHC₆H₁₃-n H COCH₂CH═CH₂ H 183 SO₃H H H SO₃H 184 SO₃H H H PO₃H₂ 185 SO₃H H H glucosyl 186 SO₃H H H mannosyl 187 SO₃H H H galactosyl 188 SO₃H H H COCH₃ 189 SO₃H H H COC₃H₇-i 190 SO₃H H H COC₁₇H₃₅-n 191 SO₃H H H COC₁₆H₃₃-n 192 SO₃H H H COC₁₈H₃₇-n 193 SO₃H H H CO(CH₂)₇CH═CHC₆H₁₃-n 194 SO₃H H H COCH═CH₂ 195 SO₃H H H COCH₂CH═CH₂ 196 PO₃H₂ H H SO₃H 197 PO₃H₂ H H PO₃H₂ 198 PO₃H₂ H H glucosyl 199 PO₃H₂ H H mannosyl 200 PO₃H₂ H H galactosyl 201 PO₃H₂ H H COCH₃ 202 PO₃H₂ H H COC₃H₇-i 203 PO₃H₂ H H COC₁₇H₃₅-n 204 PO₃H₂ H H COC₁₆H₃₃-n 205 PO₃H₂ H H COC₁₈H₃₇-n 206 PO₃H₂ H H CO(CH₂)₇CH═CHC₆H₁₃-n 207 PO₃H₂ H H COCH═CH₂ 208 PO₃H₂ H H COCH₂CH═CH₂ 209 glucosyl H H SO₃H 210 glucosyl H H PO₃H₂

TABLE 1-7 R¹ R² R³ R⁴ 211 glucosyl H H glucosyl 212 glucosyl H H mannosyl 213 glucosyl H H galactosyl 214 glucosyl H H COCH₃ 215 glucosyl H H COC₃H₇-i 216 glucosyl H H COC₁₇H₃₅-n 217 glucosyl H H COC₁₆H₃₃-n 218 glucosyl H H COC₁₈H₃₇-n 219 glucosyl H H CO(CH₂)₇CH═CHC₆H₁₃-n 220 glucosyl H H COCH═CH₂ 221 glucosyl H H COCH₂CH═CH₂ 222 COC₁₆H₃₃-n H H SO₃H 223 COC₁₆H₃₃-n H H PO₃H₂ 224 COC₁₆H₃₃-n H H glucosyl 225 COC₁₆H₃₃-n H H mannosyl 226 COC₁₆H₃₃-n H H galactosyl 227 COC₁₆H₃₃-n H H COCH₃ 228 COC₁₆H₃₃-n H H COC₃H₇-i 229 COC₁₆H₃₃-n H H COC₁₇H₃₅-n 230 COC₁₆H₃₃-n H H COC₁₆H₃₃-n 231 COC₁₆H₃₃-n H H COC₁₈H₃₇-n 232 COC₁₆H₃₃-n H H CO(CH₂)₇CH═CHC₆H₁₃-n 233 COC₁₆H₃₃-n H H COCH═CH₂ 234 COC₁₆H₃₃-n H H COCH₂CH═CH₂ 235 CO(CH₂)₇CH═CHC₆H₁₃-n H H SO₃H 236 CO(CH₂)₇CH═CHC₆H₁₃-n H H PO₃H₂ 237 CO(CH₂)₇CH═CHC₆H₁₃-n H H glucosyl 238 CO(CH₂)₇CH═CHC₆H₁₃-n H H mannosyl 239 CO(CH₂)₇CH═CHC₆H₁₃-n H H galactosyl 240 CO(CH₂)₇CH═CHC₆H₁₃-n H H COCH₃ 241 CO(CH₂)₇CH═CHC₆H₁₃-n H H COC₃H₇-i 242 CO(CH₂)₇CH═CHC₆H₁₃-n H H COC₁₇H₃₅-n 243 CO(CH₂)₇CH═CHC₆H₁₃-n H H COC₁₆H₃₃-n 244 CO(CH₂)₇CH═CHC₆H₁₃-n H H COC₁₈H₃₇-n 245 CO(CH₂)₇CH═CHC₆H₁₃-n H H CO(CH₂)₇CH═CHC₆H₁₃-n

TABLE 1-8 R¹ R² R³ R⁴ 246 CO(CH₂)₇CH═CHC₆H₁₃-n H H COCH═CH₂ 247 CO(CH₂)₇CH═CHC₆H₁₃-n H H COCH₂CH═CH₂ 248 SO₃H SO₃H SO₃H H 249 SO₃H SO₃H PO₃H₂ H 250 SO₃H SO₃H glucosyl H 251 SO₃H SO₃H mannosyl H 252 SO₃H SO₃H galactosyl H 253 SO₃H SO₃H COCH₃ H 254 SO₃H SO₃H COC₃H₇-i H 255 SO₃H SO₃H COC₁₇H₃₅-n H 256 SO₃H SO₃H COC₁₆H₃₃-n H 257 SO₃H SO₃H COC₁₈H₃₇-n H 258 SO₃H SO₃H CO(CH₂)₇CH═CHC₆H₁₃-n H 259 SO₃H SO₃H COCH═CH₂ H 260 SO₃H SO₃H COCH₂CH═CH₂ H 261 PO₃H₂ PO₃H₂ SO₃H H 262 PO₃H₂ PO₃H₂ PO₃H₂ H 263 PO₃H₂ PO₃H₂ glucosyl H 264 PO₃H₂ PO₃H₂ mannosyl H 265 PO₃H₂ PO₃H₂ galactosyl H 266 PO₃H₂ PO₃H₂ COCH₃ H 267 PO₃H₂ PO₃H₂ COC₃H₇-i H 268 PO₃H₂ PO₃H₂ COC₁₇H₃₅-n H 269 PO₃H₂ PO₃H₂ COC₁₆H₃₃-n H 270 PO₃H₂ PO₃H₂ COC₁₈H₃₇-n H 271 PO₃H₂ PO₃H₂ CO(CH₂)₇CH═CHC₆H₁₃-n H 272 PO₃H₂ PO₃H₂ COCH═CH₂ H 273 PO₃H₂ PO₃H₂ COCH₂CH═CH₂ H 274 glucosyl glucosyl SO₃H H 275 glucosyl glucosyl PO₃H₂ H 276 glucosyl glucosyl glucosyl H 277 glucosyl glucosyl mannosyl H 278 glucosyl glucosyl galactosyl H 279 glucosyl glucosyl COCH₃ H 280 glucosyl glucosyl COC₃H₇-i H

TABLE 1-9 R¹ R² R³ R⁴ 281 glucosyl glucosyl COC₁₇H₃₅-n H 282 glucosyl glucosyl COC₁₆H₃₃-n H 283 glucosyl glucosyl COC₁₈H₃₇-n H 284 glucosyl glucosyl CO(CH₂)₇CH═CHC₆H₁₃-n H 285 glucosyl glucosyl COCH═CH₂ H 286 glucosyl glucosyl COCH₂CH═CH₂ H 287 COC₁₆H₃₃-n COC₁₆H₃₃-n SO₃H H 288 COC₁₆H₃₃-n COC₁₆H₃₃-n PO₃H₂ H 289 COC₁₆H₃₃-n COC₁₆H₃₃-n glucosyl H 290 COC₁₆H₃₃-n COC₁₆H₃₃-n mannosyl H 291 COC₁₆H₃₃-n COC₁₆H₃₃-n galactosyl H 292 COC₁₆H₃₃-n COC₁₆H₃₃-n COCH₃ H 293 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₃H₇-i H 294 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₇H₃₅-n H 295 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n H 296 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₈H₃₇-n H 297 COC₁₆H₃₃-n COC₁₆H₃₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H 298 COC₁₆H₃₃-n COC₁₆H₃₃-n COCH═CH₂ H 299 COC₁₆H₃₃-n COC₁₆H₃₃-n COCH₂CH═CH₂ H 300 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n SO₃H H 301 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n PO₃H₂ H 302 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n glucosyl H 303 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n mannosyl H 304 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n galactosyl H 305 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH₃ H 306 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₃H₇-i H 307 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₇H₃₅-n H 308 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₆H₃₃-n H 309 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₈H₃₇-n H 310 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H 311 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH═CH₂ H 312 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH₂CH═CH₂ H 313 SO₃H SO₃H H SO₃H 314 SO₃H SO₃H H PO₃H₂ 315 SO₃H SO₃H H glucosyl

TABLE 1-10 R¹ R² R³ R⁴ 316 SO₃H SO₃H H mannosyl 317 SO₃H SO₃H H galactosyl 318 SO₃H SO₃H H COCH₃ 319 SO₃H SO₃H H COC₃H₇-i 320 SO₃H SO₃H H COC₁₇H₃₅-n 321 SO₃H SO₃H H COC₁₆H₃₃-n 322 SO₃H SO₃H H COC₁₈H₃₇-n 323 SO₃H SO₃H H CO(CH₂)₇CH═CHC₆H₁₃-n 324 SO₃H SO₃H H COCH═CH₂ 325 SO₃H SO₃H H COCH₂CH═CH₂ 326 PO₃H₂ PO₃H₂ H SO₃H 327 PO₃H₂ PO₃H₂ H PO₃H₂ 328 PO₃H₂ PO₃H₂ H glucosyl 329 PO₃H₂ PO₃H₂ H mannosyl 330 PO₃H₂ PO₃H₂ H galactosyl 331 PO₃H₂ PO₃H₂ H COCH₃ 332 PO₃H₂ PO₃H₂ H COC₃H₇-i 333 PO₃H₂ PO₃H₂ H COC₁₇H₃₅-n 334 PO₃H₂ PO₃H₂ H COC₁₆H₃₃-n 335 PO₃H₂ PO₃H₂ H COC₁₈H₃₇-n 336 PO₃H₂ PO₃H₂ H CO(CH₂)₇CH═CHC₆H₁₃-n 337 PO₃H₂ PO₃H₂ H COCH═CH₂ 338 PO₃H₂ PO₃H₂ H COCH₂CH═CH₂ 339 glucosyl glucosyl H SO₃H 340 glucosyl glucosyl H PO₃H₂ 341 glucosyl glucosyl H glucosyl 342 glucosyl glucosyl H mannosyl 343 glucosyl glucosyl H galactosyl 344 glucosyl glucosyl H COCH₃ 345 glucosyl glucosyl H COC₃H₇-i 346 glucosyl glucosyl H COC₁₇H₃₅-n 347 glucosyl glucosyl H COC₁₆H₃₃-n 348 glucosyl glucosyl H COC₁₈H₃₇-n 349 glucosyl glucosyl H CO(CH₂)₇CH═CHC₆H₁₃-n 350 glucosyl glucosyl H COCH═CH₂

TABLE 1-11 R¹ R² R³ R⁴ 351 glucosyl glucosyl H COCH₂CH═CH₂ 352 COC₁₆H₃₃-n COC₁₆H₃₃-n H SO₃H 353 COC₁₆H₃₃-n COC₁₆H₃₃-n H PO₃H₂ 354 COC₁₆H₃₃-n COC₁₆H₃₃-n H glucosyl 355 COC₁₆H₃₃-n COC₁₆H₃₃-n H mannosyl 356 COC₁₆H₃₃-n COC₁₆H₃₃-n H galactosyl 357 COC₁₆H₃₃-n COC₁₆H₃₃-n H COCH₃ 358 COC₁₆H₃₃-n COC₁₆H₃₃-n H COC₃H₇-i 359 COC₁₆H₃₃-n COC₁₆H₃₃-n H COC₁₇H₃₅-n 360 COC₁₆H₃₃-n COC₁₆H₃₃-n H COC₁₆H₃₃-n 361 COC₁₆H₃₃-n COC₁₆H₃₃-n H COC₁₈H₃₇-n 362 COC₁₆H₃₃-n COC₁₆H₃₃-n H CO(CH₂)₇CH═CHC₆H₁₃-n 363 COC₁₆H₃₃-n COC₁₆H₃₃-n H COCH═CH₂ 364 COC₁₆H₃₃-n COC₁₆H₃₃-n H COCH₂CH═CH₂ 365 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H SO₃H 366 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H PO₃H₂ 367 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H glucosyl 368 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H mannosyl 369 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H galactosyl 370 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COCH₃ 371 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COC₃H₇-i 372 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₇H₃₅-n 373 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₆H₃₃-n 374 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COC₁₈H₃₇-n 375 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H CO(CH₂)₇CH═CHC₆H₁₃-n 376 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COCH═CH₂ 377 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n H COCH₂CH═CH₂ 378 SO₃H SO₃H SO₃H SO₃H 379 SO₃H SO₃H SO₃H PO₃H₂ 380 SO₃H SO₃H SO₃H glucosyl 381 SO₃H SO₃H SO₃H mannosyl 382 SO₃H SO₃H SO₃H galactosyl 383 SO₃H SO₃H SO₃H COCH₃ 384 SO₃H SO₃H SO₃H COC₃H₇-i 385 SO₃H SO₃H SO₃H COC₁₇H₃₅-n

TABLE 1-12 R¹ R² R³ R⁴ 386 SO₃H SO₃H SO₃H COC₁₆H₃₃-n 387 SO₃H SO₃H SO₃H COC₁₈H₃₇-n 388 SO₃H SO₃H SO₃H CO(CH₂)₇CH═CHC₆H₁₃-n 389 SO₃H SO₃H SO₃H COCH═CH₂ 390 SO₃H SO₃H SO₃H COCH₂CH═CH₂ 391 PO₃H₂ PO₃H₂ PO₃H₂ SO₃H 392 PO₃H₂ PO₃H₂ PO₃H₂ PO₃H₂ 393 PO₃H₂ PO₃H₂ PO₃H₂ glucosyl 394 PO₃H₂ PO₃H₂ PO₃H₂ mannosyl 395 PO₃H₂ PO₃H₂ PO₃H₂ galactosyl 396 PO₃H₂ PO₃H₂ PO₃H₂ COCH₃ 397 PO₃H₂ PO₃H₂ PO₃H₂ COC₃H₇-i 398 PO₃H₂ PO₃H₂ PO₃H₂ COC₁₇H₃₅-n 399 PO₃H₂ PO₃H₂ PO₃H₂ COC₁₆H₃₃-n 400 PO₃H₂ PO₃H₂ PO₃H₂ COC₁₈H₃₇-n 401 PO₃H₂ PO₃H₂ PO₃H₂ CO(CH₂)₇CH═CHC₆H₁₃-n 402 PO₃H₂ PO₃H₂ PO₃H₂ COCH═CH₂ 403 PO₃H₂ PO₃H₂ PO₃H₂ COCH₂CH═CH₂ 404 glucosyl glucosyl glucosyl SO₃H 405 glucosyl glucosyl glucosyl PO₃H₂ 406 glucosyl glucosyl glucosyl glucosyl 407 glucosyl glucosyl glucosyl mannosyl 408 glucosyl glucosyl glucosyl galactosyl 409 glucosyl glucosyl glucosyl COCH₃ 410 glucosyl glucosyl glucosyl COC₃H₇-i 411 glucosyl glucosyl glucosyl COC₁₇H₃₅-n 412 glucosyl glucosyl glucosyl COC₁₆H₃₃-n 413 glucosyl glucosyl glucosyl COC₁₈H₃₇-n 414 glucosyl glucosyl glucosyl CO(CH₂)₇CH═CHC₆H₁₃-n 415 glucosyl glucosyl glucosyl COCH═CH₂ 416 glucosyl glucosyl glucosyl COCH₂CH═CH₂ 417 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n SO₃H 418 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n PO₃H₂ 419 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n glucosyl 420 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n mannosyl

TABLE 1-13 R¹ R² R³ R⁴ 421 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n galactosyl 422 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COCH₃ 423 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COC₃H₇-i 424 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₇H₃₅-n 425 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n 426 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₈H₃₇-n 427 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n CO(CH₂)₇CH═CHC₆H₁₃-n 428 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COCH═CH₂ 429 COC₁₆H₃₃-n COC₁₆H₃₃-n COC₁₆H₃₃-n COCH₂CH═CH₂ 430 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n SO₃H 431 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n PO₃H₂ 432 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n glucosyl 433 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n mannosyl 434 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n galactosyl 435 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH₃ 436 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₃H₇-i 437 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₇H₃₅-n 438 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₆H₃₃-n 439 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COC₁₈H₃₇-n 440 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n 441 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH═CH₂ 442 CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n CO(CH₂)₇CH═CHC₆H₁₃-n COCH₂CH═CH₂

Experiment I Comparative Example 1

Each of the frozen tobacco leaves infected with Turnip mosaic virus and Cucumber mosaic virus (Y strain) was triturated in 0.1M phosphate-buffer solution at a 10-fold amount (containing 10 mM diethyldithiocarbamic acid (DIECA)). These were defined as virus inoculation solutions A and B. These virus inoculation solutions A and B are solutions causing a 100% incidence.

Three expanded leaves per one column of Arabidopsis thaliana (Columbia) were inoculated with each virus via the aforementioned virus inoculation solutions A and B by the carborundum method.

On the 3^(rd) day and the 1^(st) day prior to the date of the virus inoculation, and on the 1^(st) day, the 3^(rd) day, the 5^(th) day, the 8^(th) day and the 10^(th) days after the date of the virus inoculation, an aqueous solution of 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation) was sprayed thereon.

On the 14^(th) day after the virus inoculation, the presence or absence of disease symptoms such as yellow mosaic of new leaves, leaf curling, and plant stunting was observed. Each of all seven columns inoculated with Turnip mosaic virus and Cucumber mosaic virus (Y strain) showed symptoms. It can be seen that the above virus inoculation solutions A and B are strong solutions in view of the fact that the inoculation with the solutions reliably causes the onset of symptoms.

Comparative Example 2

Each was dissolved in water so as to be 20 mM ascorbic acid and 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation), thereby obtaining an aqueous solution of ascorbic acid. Except that the aqueous solution of ascorbic acid was sprayed onto Arabidopsis thaliana instead of the aqueous solution of the spreading agent, in the same manner as Comparative Example 1, Turnip mosaic virus and Cucumber mosaic virus (Y strain) were inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Each of all seven columns inoculated with Turnip mosaic virus and Cucumber mosaic virus (Y strain) showed symptoms.

Example 1

Ascorbic acid 6-palmitate, a nonionic surfactant (polyoxyethylene sorbitan monolaurate) and a spreading agent (Approach BI: manufactured by Kao Corporation) were dissolved in N,N-dimethylformamide. This solution was added to water to obtain an aqueous solution of the anti-plant virus agent comprising 20 mM ascorbic acid 6-palmitate, 0.05% of a nonionic surfactant, 0.1% of a spreading agent, and 1% of N,N-dimethylformamide. Except that the aqueous solution of the anti-plant virus agent was sprayed thereon instead of the aqueous solution of ascorbic acid, in the same manner as Comparative Example 2, Turnip mosaic virus and Cucumber mosaic virus (Y strain) were inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Among each of the seven columns inoculated with Turnip mosaic virus and Cucumber mosaic virus (Y strain), each of five columns showed symptoms, and each of two columns were healthy.

Example 2

Each was added to water so as to be 20 mM ascorbic acid 2-phosphate ester 3-sodium and 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation), thereby obtaining an aqueous solution of the anti-plant virus agent. Except that the aqueous solution of the anti-plant virus agent was sprayed thereon instead of the aqueous solution of ascorbic acid, in the same manner as Comparative Example 2, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Among the seven columns inoculated with Turnip mosaic virus, five columns showed symptoms, and two columns were healthy.

About 28% of the entire Arabidopsis thaliana on which the anti-plant virus agent of the present invention was sprayed did not show symptoms and were healthy. On the other hand, for Arabidopsis thaliana on which the aqueous solution of ascorbic acid was sprayed, all columns showed symptoms. It can be seen that ascorbic acid does not have any anti-plant viral activity.

Experiment II Comparative Example 3

The frozen tobacco leaves infected with Turnip mosaic virus were triturated in 0.1M phosphate-buffer solution at a 10-fold amount (containing 10 mM DIECA). Then, this was diluted 50 times with the same buffer solution. This was defined as virus inoculation solution C.

Two expanded leaves per one column of Arabidopsis thaliana (Columbia) were inoculated with the virus via the aforementioned virus inoculation solution C by the carborundum method.

On the 3^(rd) day and the 1^(st) day prior to the date of the virus inoculation, an aqueous solution of 0.1% a spreading agent (Approach BI: manufactured by Kao Corporation) was sprayed thereon.

On the 16^(th) day after the date of the virus inoculation, the presence or absence of disease symptoms such as yellow mosaic of new leaves, leaf curling, and plant stunting was observed. Among the ten columns inoculated with Turnip mosaic virus, four columns showed symptoms, and six columns were healthy.

Comparative Example 4

Each was dissolved in water so as to be 20 mM ascorbic acid and 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation), thereby obtaining an aqueous solution of ascorbic acid. Except that the aqueous solution of ascorbic acid was sprayed onto Arabidopsis thaliana instead of the aqueous solution of the spreading agent, in the same manner as Comparative Example 3, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, two columns showed symptoms, and eight columns were healthy.

Comparative Example 5

Except that sodium ascorbate was used instead of ascorbic acid, in the same manner as Comparative Example 4, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, three columns showed symptoms, and seven columns were healthy.

Example 3

Each was added to water so as to be 20 mM ascorbic acid 2-phosphate ester 3-sodium and 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation), thereby obtaining an aqueous solution of the anti-plant virus agent. Except that the aqueous solution of the anti-plant virus agent was used instead of the aqueous solution of ascorbic acid, in the same manner as Comparative Example 4, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. All of the ten columns inoculated with Turnip mosaic virus were healthy.

Example 4

Each was added to water so as to be 20 mM ascorbic acid 2-glucoside and 0.1% of a spreading agent (Approach BI: manufactured by Kao Corporation), thereby obtaining an aqueous solution of the anti-plant virus agent. Except that the aqueous solution of the anti-plant virus agent was used instead of the aqueous solution of ascorbic acid, in the same manner as Comparative Example 4, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, one column showed symptoms, and nine columns were healthy.

From the above, it can be seen that the aqueous solution of the anti-plant virus agent of the present invention showed a preventive value of 75% or more, and exhibits preventive effects against plant virus diseases. On the other hand, it can be seen that the ascorbic acid and the salts thereof do not have any anti-plant viral activity.

Experiment III Comparative Example 6

A nonionic surfactant (polyoxyethylene sorbitan monolaurate) and a spreading agent (Approach BI: manufactured by Kao Corporation) were dissolved in N,N-dimethylformamide. This solution was added to water to obtain an aqueous solution comprising 0.05% of a nonionic surfactant, 0.1% of a spreading agent, and 1% of N,N-dimethylformamide.

Two expanded leaves per one column of Arabidopsis thaliana (Columbia) were inoculated with the virus via the aforementioned virus inoculation solution C by the carborundum method.

On the 1^(st) day, the 4^(th) day, the 7^(th) day and the 10^(th) day after the date of the virus inoculation, the aforementioned aqueous solution was sprayed thereon.

On the 16^(th) day after the date of the virus inoculation, the presence or absence of disease symptoms such as yellow mosaic of new leaves, leaf curling, plant stunting was observed. Among the ten columns inoculated with Turnip mosaic virus, three columns showed symptoms, and seven columns were healthy.

Example 5

Ascorbic acid 6-palmitate, a nonionic surfactant (polyoxyethylene sorbitan monolaurate) and a spreading agent (Approach BI: manufactured by Kao Corporation) were dissolved in N,N-dimethylformamide. This solution was added to water to obtain an aqueous solution of the anti-plant virus agent comprising 20 mM ascorbic acid 6-palmitate, 0.05% of a nonionic surfactant, 0.1% of a spreading agent, and 1% of N,N-dimethylformamide.

Except that the aqueous solution of the anti-plant virus agent was sprayed onto Arabidopsis thaliana instead of the aforementioned aqueous solution, in the same manner as Comparative Example 6, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of the symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, one column showed symptoms, and nine columns were healthy.

Example 6

Except that ascorbic acid 2,6-dipalmitate was used instead of ascorbic acid 6-palmitate, in the same manner as Example 5, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of the symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, one column showed symptoms, and nine columns were healthy.

Example 7

Except that ascorbic acid 6-stearate was used instead of ascorbic acid 6-palmitate, in the same manner as Example 5, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of the symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, one column showed symptoms, and nine columns were healthy.

Example 8

Except that ascorbyl 2,3,5,6-tetrahexyldecanoate was used instead of ascorbic acid 6-palmitate, in the same manner as Example 5, Turnip mosaic virus was inoculated onto Arabidopsis thaliana, and then the onset of the symptoms was examined. Among the ten columns inoculated with Turnip mosaic virus, one column showed symptoms, and nine columns were healthy.

From the above, it can be seen that the anti-plant virus agent of the present invention exhibits therapeutic effects against plant virus diseases.

Experiment IV Comparative Example 7

The frozen tobacco (Nicotiana benthamiana) infected with Tomato aspermy virus (V strain) was triturated in 0.1M phosphate-buffer solution at a 10-fold amount (containing 10 mM DIECA), and was filtered through a double gauze and the filtrate was defined as virus inoculation solution D. Onto fully expanded leaves of the seedling stage of tomato (cultivar: Beiju) after a period of two weeks from seeding, the virus inoculation solution D was inoculated by physical application via the carborundum method.

After the virus inoculation, as a result of examination of disease symptoms over time, mosaic or leaf curling could be recognized after the 5^(th) day, and lethal necrosis symptoms were shown after the period of two weeks, and all of the five columns inoculated with Tomato aspermy virus (V strain) withered.

Example 9

200 mM of ascorbic acid 6-palmitate was dissolved in N,N-dimethylformamide. This solution was diluted 100 times with distilled water to obtain an aqueous solution of the anti-plant virus agent comprising 2 mM ascorbic acid 6-palmitate and 1% of N,N-dimethylformamide. In the same manner as Comparative Example 7, the tomato was inoculated with tomato aspermy virus (V strain). During the two weeks from the date of virus inoculation, the aforementioned aqueous solution was sprayed thereon every day, and disease symptoms were examined over time.

On the 30^(th) day after the date of the inoculation, the presence or absence of disease symptoms was observed, and as a result, among the four columns inoculated with Tomato aspermy virus (V strain), two columns withered, and two columns were healthy. With regard to the two healthy columns, they showed more vigorous growth compared with the tomato on which the virus had not been inoculated and ascorbic acid 6-palmitate had not been sprayed.

INDUSTRIAL APPLICABILITY

The anti-plant virus agent of the present invention has a high anti-plant viral activity. The application of the anti-plant virus agent of the present invention to normal plants makes it possible to effectively prevent infection by plant viruses (preventive effect). In addition, the application of the anti-plant virus agent of the present invention to plants infected with plant viruses makes it possible to suppress the onset of plant diseases (therapeutic effect). Given the above, the present invention is industrially very useful. 

1. An anti-plant virus agent comprising at least one compound selected from the group consisting of ascorbic acid derivatives represented by Formula I and salts thereof□

wherein, R¹ to R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹, wherein R¹¹ represents an unsubstituted or substituted C1-30 alkyl group, or an unsubstituted or substituted C2-30 alkenyl group; with the proviso that R¹ to R⁴ may not all be hydrogen atoms at the same time.
 2. The anti-plant virus agent according to claim 1, wherein, in Formula (I), R¹ and R² represent a hydrogen atom, and R³ and R⁴ each independently represents a hydrogen atom, —SO₃H, —PO₃H₂, a glycosyl group, or —COR¹¹, wherein R¹¹ represents the same meaning as described above.
 3. The anti-plant virus agent according to claim 1, wherein, in Formula (I), R¹ is —COR¹¹, wherein R¹¹ represents the same meaning as described above, and R² to R⁴ represent a hydrogen atom. 